Premium
Unusual Reactivity of Dimethylsulfoxonium Methylide with Esters
Author(s) -
Leggio Antonella,
De Marco Rosaria,
Perri Francesca,
Spinella Mariagiovanna,
Liguori Angelo
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101031
Subject(s) - chemistry , enantiopure drug , racemization , reactivity (psychology) , hydrolysis , cleavage (geology) , reagent , organic chemistry , substrate (aquarium) , reaction mechanism , combinatorial chemistry , catalysis , enantioselective synthesis , medicine , oceanography , alternative medicine , geotechnical engineering , pathology , fracture (geology) , geology , engineering
The dimethylsulfoxonium methylide was treated with esters under mild conditions to rapidly afford the corresponding carboxylic acids at room temperature. Moreover, by performing the procedure on enantiopure substrates, it was demonstrated that the reaction occurs without racemization. 18 O‐labeled reagents showed that the reaction does not proceed through an ester hydrolysis mechanism. The reactions are characterized by an unusual reactivity of the dimethylsulfoxonium methylide. This methodology is general and can be considered a valid alternate route for ester cleavage when a substrate is sensitive to hydrolysis conditions.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom